The third or fifth son of Kaihô Tsunachika, a senior retainer of the Asai of Ômi province, he was made a ward of Tôfukuji at a young age, and was thus spared the fate of his brothers and father, who were killed in battle serving Asai Nagamasa, who was defeated by Oda Nobunaga in 1573. It was at this time, following the defeat and destruction of his family, that Yûshô, at age 41, first left the temple and began his career as an artist.

He is said to have studied under the famous painter Kanô Motonobu, though it may have in fact been Motonobu's son Eitoku. He was patronized by Toyotomi Hideyoshi and the Emperor Go-Yôzei, and developed contacts and connections among many circles of Kyoto society, including nobility, samurai, artists, and Zen monks. His paintings were often colorful and in the Kanô style, though he was also proficient in the traditional monochromatic ink style employed by many Zen monks/painters.

Around 1599, he executed a set of fusuma painting for the Zenkoan, a sub-temple of Kennin-ji, depicting the so-called "three friends," bamboo, plum, and pine.